Kaupo Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Tim & Nat ✈

Top hotels in Kaupo

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
Fully refundableReserve now, pay when you stay
The price is 22.456.496 ₫ per night from 20 Aug to 21 Aug
22.456.496 ₫
28.039.654 ₫ total
20 Aug - 21 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Amazing and relaxing resort
"It was an amazing boutique resort the property is beautiful and very relaxing a different vibe from the other Wailea resorts the staff is great and the amenities are nice including the shuttles to anywhere in the Wailea area. Definitely would come back and say if you get a chance to check it out ..."

Reviewed on 23 Jul 2025

Hotel Wailea, Relais & Chateaux - Adults Only
Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

4 out of 5
5031 Hana Hwy, Hana, HI
Fully refundableReserve now, pay when you stay
The price is 13.004.640 ₫ per night from 17 Sept to 18 Sept
13.004.640 ₫
16.338.869 ₫ total
17 Sept - 18 Sept
includes taxes & fees
9/10 Wonderful! (992 reviews)
"Beautiful property with amazing views. We were complimentary upgraded to our own cottage with two adjoining rooms for our family of 4...it was perfect. Would definitely stay here again."

Reviewed on 14 Aug 2025

Hana-Maui Resort, a Destination by Hyatt Residence
Wailea Ekolu - CoralTree Residence Collection

Wailea Ekolu - CoralTree Residence Collection

3.5 out of 5
10 Wailea Ekolu Place, Kihei, HI
The price is 8.656.625 ₫ per night from 19 Aug to 20 Aug
8.656.625 ₫
20.655.998 ₫ total
19 Aug - 20 Aug
includes taxes & fees
8.8/10 Excellent! (258 reviews)
"property was clean and very accessible to what we were doing."

Reviewed on 25 Jun 2025

Wailea Ekolu - CoralTree Residence Collection
See all 149 properties in Kaupo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Maui Garden Of Eden - Botanical Gardens & Arboretum

Maui Garden Of Eden - Botanical Gardens & Arboretum

Explore the great outdoors at Maui Garden Of Eden - Botanical Gardens & Arboretum, a lovely green space in Hana. Wander the beaches and seaside in this romantic area.

Maui Garden Of Eden - Botanical Gardens & Arboretum
Waianapanapa State Park

Waianapanapa State Park

5/5(1 review)

If a restful holiday is part of your travel plans, Waianapanapa State Park might be the perfect place to visit during your trip to Hana. Wander the seaside and gardens in this romantic area.

Waianapanapa State Park
Hamoa Beach

Hamoa Beach

If a restful holiday is part of your travel plans, Hamoa Beach might be the perfect place to visit during your trip to Hana. Amble around this romantic area's seaside or seek out the yoga studios.

Hamoa Beach

Frequently asked questions

How much does a Kaupo holiday package cost?
You'll find cheap prices on Expedia for your Kaupo break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your holiday to Kaupo costs.
What are the cheapest months to go to Kaupo?
January, February and June are the best times to look for cheap Kaupo holiday packages. Travelling in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Kaupo?
With a well-planned schedule, you can easily hit the most popular Kaupo sights in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Kaupo holiday for longer.
How to find the best Kaupo package deals?
Use Expedia's filters to find some tempting Kaupo package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Kaupo package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Kaupo holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation and flights individually. Better still, you can tailor your Kaupo escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Kaupo?
If you're planning an impromptu Kaupo adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Kaupo?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to holiday in Kaupo.
  2. Budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Kaupo.
  3. Work out your trip length: Think about how much time you want to spend exploring Kaupo. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Kaupo holiday package.